(1-benzyl-1H-1,2,3-triazol-4-yl)(4-nitrophenyl)methanone | 1253116-77-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-benzyl-1H-1,2,3-triazol-4-yl)(4-nitrophenyl)methanone
• 英文别名: (1-Benzyltriazol-4-yl)-(4-nitrophenyl)methanone；(1-benzyltriazol-4-yl)-(4-nitrophenyl)methanone
• CAS: 1253116-77-6
• 化学式: C₁₆H₁₂N₄O₃
• 分子量: 308.296
• InChiKey: IEGSEBUZVXSEKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基苯甲酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 silver fluoride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 生成 (1-benzyl-1H-1,2,3-triazol-4-yl)(4-nitrophenyl)methanone
  参考文献：
  名称：

  An efficient and high-yielding one-pot synthesis of 4-acyl-1,2,3-triazoles via triisopropylsilyl-protected ynones

  摘要：

  A practical and efficient process has been developed for the synthesis of 1-substituted 4-acyl-1H-1,2,3-triazoles using a three-step one-pot synthetic approach. This transformation involves an initial preparation of triisopropylsilyl (TIPS)-protected ynones from acid chlorides and TIPS-acetylene, followed by a AgF-mediated TIPS deprotection and Cu-catalyzed Huisgen cycloaddition. The increased chemical stability of TIPS-protected ynones was an important factor in the high overall product yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.025

文献信息

• Copper-Catalyzed Oxidative Cross-Dehydrogenative Coupling/Oxidative Cycloaddition: Synthesis of 4-Acyl-1,2,3-Triazoles
  作者：Yi Liu、Gang Nie、Zhongzhen Zhou、Lihui Jia、Yunfeng Chen

  DOI：10.1021/acs.joc.7b01429

  日期：2017.9.1

  A copper-catalyzed three-component reaction of methyl ketones, organic azides, and various one-carbon (C1) donors was developed that provides 4-acyl-1,2,3-triazoles in moderate to good yields. While DMF, DMA, TMEDA, or DMSO can serve as the C1 donor, best yields were obtained using DMF. The transformation is proposed to proceed via an oxidative C–H/C–H cross-dehydrogenative coupling followed by an

  开发了铜催化的甲基酮，有机叠氮化物和各种单碳（C1）供体的三组分反应，该反应以中等至良好的产率提供了4-酰基-1,2,3-三唑。虽然DMF，DMA，TMEDA或DMSO可以用作C1供体，但使用DMF可获得最佳产量。有人建议通过氧化C–H / C–H交叉脱氢偶合，然后进行氧化1,3-偶极环加成反应进行转化。
• Promotion of 1,3-dipolar cycloaddition between azides and β-enaminones by deep eutectic solvents
  作者：Marcos Antonio Pinto Martins、Guilherme Caneppele Paveglio、Leticia Valvassori Rodrigues、Clarissa Piccinin Frizzo、Nilo Zanatta、Helio Gauze Bonacorso

  DOI：10.1039/c5nj03654b

  日期：——

  The metal-free, high selectivity and efficient synthesis of 4-acyl triazoles in a DES (ChCl:ethylene glycol) is reported.

  报道了在DES（ChCl：乙二醇）中无金属、高选择性和高效合成4-酰基三唑的方法。
• One-Pot Three-Step Synthesis of 1,2,3-Triazoles by Copper-Catalyzed Cycloaddition of Azides with Alkynes formed by a Sonogashira Cross-Coupling and Desilylation
  作者：Frédéric Friscourt、Geert-Jan Boons

  DOI：10.1021/ol1022036

  日期：2010.11.5

  A microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition sequence was developed for the convenient preparation of 1,4-disubstituted 1,2,3-triazoles starting from a range of halides, acyl chlorides, ethynyltrimethylsilane, and azides.
• An efficient and high-yielding one-pot synthesis of 4-acyl-1,2,3-triazoles via triisopropylsilyl-protected ynones
  作者：Soonho Hwang、Hoon Bae、Sumin Kim、Sanghee Kim

  DOI：10.1016/j.tet.2011.12.025

  日期：2012.2

  A practical and efficient process has been developed for the synthesis of 1-substituted 4-acyl-1H-1,2,3-triazoles using a three-step one-pot synthetic approach. This transformation involves an initial preparation of triisopropylsilyl (TIPS)-protected ynones from acid chlorides and TIPS-acetylene, followed by a AgF-mediated TIPS deprotection and Cu-catalyzed Huisgen cycloaddition. The increased chemical stability of TIPS-protected ynones was an important factor in the high overall product yield. (C) 2011 Elsevier Ltd. All rights reserved.